Synthesis of chiral alcohol and ester pheromones through enzyme-catalysed hydrolysis using Pseudomonas fluorescens lipase: preparation of (2R,6S,10S)-6,10–14-Trimethylpentadecan-2-ol and the propionate of (2R,8R)-8-methyldecan-2-ol

Abstract

(2R,6S,10S)-6,10,14-Trimethylpentadecan-2-ol [(2R,6S,10S)-15], one of the stereoisomers of the sex pheromone of Corcyra cephalonica Stainton, was synthesized in highly optically pure form by the hydrolysis of the 2,2,2-trichloroethyl carbonate of (2RS,6S,10S)-6,10,14-trimethylpentadecan-2-ol [(2RS,6S,10S)-15a] with Pseudomonas fluorescens lipase. The same method led to stereochemically pure (2R,8R)-8-methyldecan-2-yl propionate [(2R,8R)-24], which is a component of the sex pheromone of Diabrotica species.